Tottenham's worst ever transfer window will finally release its hold on the club this summer

If you want the perfect example of a transfer window that promised so much yet still haunts a football club to this day, just look at Tottenham's work in the summer of 2019.

It came after two windows - summer and winter - in the 2018/19 season without a single incoming transfer, a year that, coupled with the Champions League final defeat, left a frustrated Tottenham fanbase, a jaded manager in Mauricio Pochettino and feeling within the playing squad that the club had peaked in failing to reach the top on that night in Madrid.

A key opportunity to replenish a squad that needed rejuvenation had not been taken, with claims inside the club at the time that money was tight with the funds tied up in the construction of the club's new stadium. In hindsight, the sale of one of the team's big stars, which Spurs were desperate to avoid, might have funded the rebuild required at a club that was run to live within its means.

Instead hopeful bids in the summer of 2018 had been made for British stars such as Jack Grealish, James Ward-Prowse and boyhood Spurs fan Ezri Konsa but none were at the required level to get the deals over the line.

The Grealish move in particular was a long drawn out affair that ended embarrassingly when Aston Villa received new financial backing and no longer needed to sell the midfielder, who had already waved goodbye to the fans after thinking he was leaving for Tottenham. That failed move had particularly frustrated Pochettino.

So belatedly Spurs looked to address that in the summer of 2019 with moves for exciting young stars to breathe life and energy back into Pochettino's team.

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During the season, the Argentine had been a big fan of Ajax star Frenkie de Jong and felt the then 21-year-old Dutchman would be the perfect fit within his system. In the first half of the campaign, Spurs chased the talented young midfielder ahead of a potential move the following summer but they came up against a major foe in the shape of Barcelona, who were able to agree a deal with Ajax worth €86million including add-ons (£73million in today's money).

With De Jong out of the picture, Pochettino and Spurs' technical performance director Steve Hitchen, focused their attention on 22-year-old Lyon midfielder Tanguy Ndombele, who had been a close second choice to the Dutchman and became top choice that summer after that Barcelona intervention.

There were some reservations about the young French midfielder and his motivation levels in the past. However, the signs appeared to be that Ndombele had pushed on and that under Pochettino he would mature and flourish as others had done. Spurs chairman Daniel Levy came up against a Lyon president in Jean-Michel Aulas who would not roll over on the price tag for a player who many of Europe's top clubs were considering.

After plenty of toing and froing Lyon announced the deal with Spurs on July 2, 2019 with a press release that stated the price as "€60million, with incentives which could reach as high as €10million", worth £59.5million in today's money.

Ndombele joined up with Pochettino's pre-season and headed off on tour to Singapore and Shanghai, but would be the club's only senior signing for much of their preparations for that campaign. The Spurs boss grew visibly more and more frustrated during that pre-season at the lack of progress with adding to his depleted squad, with Kieran Trippier joining Atletico Madrid and Mousa Dembele having left in January of that year.

Spurs did sign Jack Clarke on July 12, a young Leeds winger tracked by the club but not wanted by Pochettino for his first team set-up at that point. The 18-year-old was awkwardly sent back to the Elland Road on loan, despite the fact that Marcelo Bielsa's team would end up having too many loan players and he would struggle for game time.

Tottenham had also been keeping an eye on Hull City's Jarrod Bowen as an alternative, but with Clarke's price tag half of Bowen's for a player deemed to have more potential it was the Leeds teenager who was signed. As with all of the transfers in that window for Spurs, history and fate would slap Tottenham in the face.

Pochettino wanted another attacking midfielder or number 10 to bolster his Champions League finalists. His and the club's wish-list contained Grealish (again), Sporting midfielder Bruno Fernandes, Juventus forward Paulo Dybala and Real Betis' Argentine Giovani Lo Celso.

Grealish was set as off-limits though this time by Villa with all bids to be rejected that summer from anyone for the midfielder. Tottenham made an attempt to sign Fernandes, but their attempts fell below what was required.

"Obviously I wanted to go to the Premier League. The manager, Mauricio Pochettino, was the one who wanted me there. It was a good offer but Sporting tried their best to keep me," Fernandes would say three years later while at Manchester United. "The president (Frederico Varandas) spoke with me but he spoke with me on the wrong day. It was the day after they decided to refuse the offer from Tottenham and I was really angry. Luckily for me, the manager (Marcel Keizer) was the right one at the right time."

News of a potential move for Dybala emerged while Spurs were in Shanghai that summer. Juventus' transfer chief Fabio Paratici, who three years later would take on a similar role at Tottenham, was looking to move on the Argentine striker for the right price as he was not believed to be a major fan of the young forward and the north London club were willing to get a deal done.

"I was close to leaving. That was in the club's thinking, I knew. Until the last minute, we were waiting," Dybala would say later that season.

However, exactly how the deal ended up being scuppered after weeks of negotiations differs depending on who you speak to among those involved in and around it. The most offered reason is those infamous image rights, which Dybala had reportedly sold to a company owned by a former agent and Spurs would have to reach a costly financial agreement with them since image rights would not be legally recognised by the Premier League. Those in Italy would instead claim that Juventus ended up pulling the plug on the deal because they could not sign Romelu Lukaku as a replacement because he was heading to Inter.

In the meantime, Spurs were working on the next name on their list - Lo Celso - in order to push that through should the Dybala deal fail to come to pass.

That deal was less complex and was agreed, although it ended up being a loan with an option to buy, which was eventually taken up in January of the next year. In total the deal for the Argentine was believed to be worth around £55million to Betis including add-ons and the loan fee.

That deal was agreed on the Premier League's earlier August 8 deadline day that year, along with a late move for one of the most wanted young players in the English game - Ryan Sessegnon.

Most of the top teams in the Premier League and across Europe wanted to sign the 19-year-old from Fulham and everyone inside Tottenham, including Pochettino, was excited about the move, which cost the club around £25million and academy product Josh Onomah moving in the opposite direction.

However, Fulham had not been impressed by Spurs' drawn-out handling of the transfer, with vice-chairman Tony Khan telling his club's fans in a statement: "We heard from them [Tottenham] for the first time two weeks before the close of the window. We had been making all our deals under the assumption that Ryan could wind the contract down and they were not going to offer us anything. I was totally prepared for that.

"It seemed like it might be a likely scenario when he still had not heard from them a couple of weeks out, which is why I was doing loan deals where we knew the club would compliant with Financial Fair Play [FFP] rules. We had got three of our top four targets on loan but there was still a lot of uncertainty about what we could do in the rest of the window after we got Ivan Cavaleiro, Anthony Knockaert and Harry Arter.

"It turned out we were not able to buy any players because this transaction had been held up. And when I finally got an offer it was so ridiculously low that I had to make it super clear that we were not going to take a penny less than our asking price, which is exactly what we got. If it was a penny less than our asking price I was perfectly fine for the player to wind his contract down."

He added: "We were so far apart that 24 hours before the deadline I was prepared for Ryan to stay at Fulham this year. We were going to get every penny that we asked for, and we got every penny we asked for. I wish it had not taken so long.

"People have said ‘you knew you were going to get the money, why did you not go out and spend it?’ No, until we had every penny in hand I was not going to go out and spend it. It was not until the middle of the afternoon on deadline day that we actually had a signed agreement. There were multiple breakdowns in the closing days.

"I was glad we had done some deals early [in the window], but the stuff we did on deadline day was greatly impacted by the sale that went through late on deadline day."

Spurs were missing the striker Pochettino wanted to back-up Harry Kane, with Fernando Llorente's contract expiring and Vincent Janssen having left for Mexican side Monterrey, but on the whole the signing of the three exciting young players from Lyon, Real Betis and Fulham were a welcome boost for a flagging squad.

Tottenham had spent money as well, to somewhat make up for those two empty windows, with eventually around £150million in total put forward including potential add-ons, not to mention the wages involved.

Yet history now looks back on that window as one of the worst, if not the worst, window the club has ever spent money in, not helped by the fact that the manager they were bought for was sacked within a few months.

The four players bought in that summer of 2019, in the time since, have started just 104 Premier League matches between them in the past half a decade. Ndombele managed 46 of those, Lo Celso 32, Sessegnon 26 and Clarke not a single one and all four were sent on loans galore across the bunch.

There were some mitigating factors, Sessegnon and Lo Celso were hampered by constant injuries that fragmented their seasons, the former in particular faced with horrendous hamstring problems. Ndombele was hampered by his own ability to convince a string of managers that he could maintain a consistent level of motivation or tactical discipline, while Clarke was unfortunate to be a club signing a manager was not looking for, not the first time that has happened at Tottenham or any club and likely not the last.

Clarke has gone on to make a success of his career at Sunderland and is being tipped to return to the Premier League this summer, while the desperately unfortunate Sessegnon has now left Tottenham after the club chose not to take up the final year option to extend his contract by another 12 months after a final season which brought just eight minutes of game time for the 24-year-old full-back.

Ndombele and Lo Celso are still on the books but both are expected to leave this summer. Ndombele has bounced around Europe on loan, winning league titles at Napoli and Galatasaray without needing to start barely any matches to do so, while Lo Celso gave some hope that he was going to finally bring redemption for that summer of 2019 under Postecoglou this season but injuries and a lack of chances saw that fritter away.

Spurs should still get a decent sum for Lo Celso with the midfielder on Copa America duty with Argentine but they are going to struggle to palm the once-so-exciting Ndombele off on somebody this summer, so low has the 27-year-old's stock fallen. He has become the club's most expensive mistake.

What came next immediately after 2019 was barely much better. In the 2020 January window, Hitchen pushed for Steven Bergwijn's signing and a combination of Jose Mourinho and super agent Jorge Mendes brought Gedson Fernandes to N17. Neither are at the club any longer.

The 2020 summer window was another exciting one with signings galore, headlined by the return of Gareth Bale and supported by Sergio Reguilon, Matt Doherty, Pierre-Emile Hojbjerg, Joe Rodon, Joe Hart and Carlos Vinicius. Only Hojbjerg would go on to become a regular starter beyond that season and will likely leave this summer along with Reguilon and Rodon, meaning another window's worth of players have come and gone.

Still it will not top the money and talent that came and went the previous year. When Tanguy Ndombele and Giovani Lo Celso depart then Tottenham will finally be rid of the spectre of that 2019 summer transfer window and the thought of what might have been.

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